Tert-Butylamine → ({3-[(1S)-2-tert-Butoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzoyl}oxy)(tert-butyl)ammonium

HRID 644094Notes

Reaction equation

HRID 644094 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[C:6]([O:10][CH2:11][C@H:12]([CH3:34])[O:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)[CH:22]=1)[C:17]([OH:19])=[O:18])([CH3:9])([CH3:8])[CH3:7]>CC(OC)(C)C>[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[C:6]([O:10][CH2:11][C@H:12]([CH3:34])[O:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)[CH:22]=1)[C:17]([O:19][NH2+:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:18])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 592633093-[(1S)-2-tert-Butoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzoic acid

Product 2

HCID 6385Tert-ButylamineHCID 86622613({3-[(1S)-2-tert-Butoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzoyl}oxy)(tert-butyl)ammoniumYield 181.5%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

A solution of tert-butylamine was prepared by charging tert-butylamine (0.31 L, 2.94 mol) to a reaction vessel containing MTBE (2.27 L). The solution was stirred at ambient temperature and then charged into a second reaction vessel containing 3-[(1S)-2-tert-butoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzoic acid (1.13 Kg, 267 mol) and MTBE (2.54 L). The temperature was maintained between 20-30° C. during the addition, the residual tert-butylamine was washed in with MTBE (0.57 L). The reaction mixture was heated to 38-40° C. for 3 hours under a nitrogen atmosphere. The reaction mixture was cooled to 18-25° C. over 1-2 hours and then held until crystallisation occurred. The product was isolated by filtration washed twice with MTBE (2.28 L), and dried in a vacuum oven at 38-40° C. This resulted in (1.32 Kg, 100% yield) of the title compound.

Workup

  1. additioncharged into a second reaction vessel
  2. temperatureThe temperature was maintained between 20-30° C. during the addition
  3. washthe residual tert-butylamine was washed in with MTBE (0.57 L)
  4. temperatureThe reaction mixture was heated to 38-40° C. for 3 hours under a nitrogen atmosphere
  5. temperatureThe reaction mixture was cooled to 18-25° C. over 1-2 hours
  6. customheld until crystallisation
  7. customThe product was isolated by filtration
  8. washwashed twice with MTBE (2.28 L)
  9. customdried in a vacuum oven at 38-40° C

Sources & evidence

ORD record
ord-61650a56ca9e426cbea14357d7e737dc
Source dataset
uspto-grants-2010_04
Patent number
US07700640B2

Reaction notes

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